1,4-Butanediol, 2-methylene- synthesis
- Product Name:1,4-Butanediol, 2-methylene-
- CAS Number:55881-94-2
- Molecular formula:C5H10O2
- Molecular Weight:102.13
53720-10-8
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Yield:55881-94-2 98%
Reaction Conditions:
Stage #1: diisopropyl 2-methylidenebutanedioatewith aluminium hydride in diethyl ether at -30;
Stage #2: with sulfuric acid in diethyl ether;water at -30;
Steps:
4.3. 2-Methylene-1,4-butanediol 2
A suspension of LAH (11.4 g, 0.30 mol) in Et2O (200 mL) at 0 °C was added to a stirred solution of AlCl3 (13.4 g, 0.10 mol) in dried Et2O (300 mL). After 30 min, the ester (32.1 g, 0.15 mol) dissolved in Et2O (100 mL) was slowly added at -30 °C. The reaction was immediately stopped after the addition of the ester, by adding 10% of aq H2SO4. The reaction mixture was extracted with EtOAc, and the organic phases were combined and washed with aq NaHCO3, dried over MgSO4 and evaporated to yield diol 2 (15.3 g, 98%); 1H NMR (300 MHz, CDCl3) δ: 5.07 (s, 1H), 4.92 (s, 1H), 4.03 (s, 2H), 3.69 (t, J = 6.0 Hz, 2H), 2.31 (t, J = 6.0 Hz, 2H); the 1H NMR spectrum was identical to that reported in the literature.21
References:
Kim, Youngju;Watanabe, Hidenori;Kim, Bieong-Kil;Seu, Young-Bae [Tetrahedron Asymmetry,2011,vol. 22,# 16-17,p. 1658 - 1661] Location in patent:experimental part
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